Lecture 29
• Hand in LP 9/10
• Quiz 8 Review
• Course evaluation
Next Lecture:
Quiz 8
This Week in Lab:
• Synthetic #2 Final Report Due
• Remember to bring all graded PreLabs and Aldrich to lab
• Clean up and check-out!
Quiz 8
Questions on:
• Reactions/synthetics that were gone over in class
• Mechanisms of reactions from lecture
• Special topics:
• Drug discovery
• Retrosynthetic analysis
• Molecular modification
• Sweeteners (saccharin, aspartame, sucralose)
• Lab application questions - comprehensive
Quiz 8
Reactions:
Nitrile reaction (synthesis of creatine)
Substitution (Sn2) reactions: (plant hormone & norleucine)
Acyl substitution reaction (synthesis of “OFF”)
Reductions:
• Of alkenes (hydrogenation of olive oil)
• Of carbonyls (with hydride ion)
Esterifications:
• Transesterification (synthesis of 3-carbethoxycoumarin)
• Fisher esterification (benzocaine & others)
• Alternative (with anhydrides; synthesis of aspirin)
Enolate Chemistry:
• Aldol Condensation (synthesis of 3-carbethoxycoumarin)
Quiz 8
Reactions:
Be able to draw out the mechanisms of only those
that were given in lecture. Know the reagents
used for each reaction.
Special topics:
• Drug discovery process (nakadomarin A & taxol)
• Retrosynthetic analysis
• Molecular modification (cocaine & related compounds)
• Sweeteners: know the synthetic pathways to aspartame
and sucralose
Be able to identify a compound
Quiz 8
Lab Application Sample Questions:
1. Susie is running out of time, but she wants to obtain a melting point
reading before the end of the lab period. She turns the dial on the
Mel-Temp up to 7, and the temperature rises at about 10˚C per minute.
Is this proper technique to obtain an accurate melting point?
Why or why not?
2. You run a TLC to determine if your reaction has run to
completion, and you observe the results shown on the plate below.
Did your reaction run to completion? How do you know?
SM
CO
Rxn
Practice Quiz Problems
1. NaBH4
H OH
2. H+
O
1.
O
NaOH
H
H
H
2.
3.
H+
LP 9/10
#1
O
O
O
OH
H+
CH3
H2 (g)
CH3
Pd
+ H2O
LP 9/10
#2. Identify the nucleophile & electrophile. Circle the
sites of reactivity on each.
H2N C N
+
H
N
O
OH
NaCl
NH4OH
H2O
NH
H2N
O
N
creatine
OH